


Hoo-Doo You-Doo

by VioletHyena



Category: Supernatural
Genre: Crossdressing, Drag Queens, M/M
Language: English
Status: Completed
Published: 2014-05-01
Updated: 2014-05-01
Packaged: 2018-01-21 12:00:55
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,013
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1549760
Author URL: https://archiveofourown.org/users/VioletHyena/pseuds/VioletHyena
Summary: <blockquote class="userstuff">
              <p>Sam's secret is that he's a drag queen. Gabriel meets his alter ego, Doe Adeer, and they hit it off very well. Sam is nervous about telling Gabriel who he is, but Gabriel might figure it out himself first.</p>
            </blockquote>





	Hoo-Doo You-Doo

**Author's Note:**

> me and rivertem (tumblr) started discussing how pretty Sam was and how he needed to be in pretty things. So I put Sam in pretty things, and it turned out lovely.
> 
> If you liked my fanfiction, please check out My Books! A link can be found at the end of my AO3 profile page.

“Hey, Sam, you working late tonight?” Gabriel peaked into the small law office, knocking on the already open door. Sam was tidying up his desk; not that there was anything much to mess up on  _ Mr. Winchester _ 's desk. He was just putting case files back into his cabinet drawer.

 

Sam looked up, in his crisp suit and dress shoes. His longer hair was brushed back, often tied in a low ponytail to remain professional looking. He'd given up trying to tell Gabriel to call him Mr. Winchester after the first week and Gabriel did not respond to Mr. Shurley (that was his father's name!). Not that he was a lawyer, no, Gabriel was the maintenance man who kept the office clean and functioning properly. But he made a constant visit to Sam's office to entertain himself and had formed a long bond with Sam's radiator; with having to fix it so often. Sam wasn't quite as stuck up as some of the other lawyers in the building; much better looking, too. 

 

“No, I'm going home to relax for the night,” Sam told him, tense shoulders relaxing.

 

“You seem to do that every week,” Gabriel grumbled. “It's Friday, technically the weekend. We should hit a bar or two.”

 

“No, thank you, Gabriel,” Sam gave an almost shy smile. “Friday is my night in with a good book and a bubble bath.” Gabriel's brows rose because he wondered if Sam's tub was big enough for two. Apart from his own perverse thoughts, it was a down right crime that the man didn't go out and have fun. Most of all always skipping fun with Gabriel himself.

 

“Fine, be a party pooper.” Gabriel gave a wave as he walked towards the exit. “See you Monday.”

 

“See you Monday,” Sam replied in kind and gathered his things to also leave.

 

 

* * *

 

Sam did in fact go home, but he didn't really curl up with a good book like he said he would. That was just his alibi for what he really did on his Friday nights. When Sam got in, he removed his suit and shoes. Then he put on casual clothes after a quick shower. He was indeed going out, but he also wasn't going to dress at home. He didn't want his neighbors seeing a lawyer going home at night and then a woman going out perhaps a couple hours later. No, he was very shy about that. Instead he picked what he wanted for that night's dress, shoes, makeup, and hair extensions, then packed them neatly away in a suitcase. He drove down town to the local drag show bar with a very obnoxious neon sign that read 'Hoo-Doo Yoo-Doo' on the brick building.

 

He went into the backstage area, nodding to the security guard, Mr. Golem, who just shrugged him in. He was definitely not a newbie there. He had actually started there in college, but he always kept his personal life and work life separate. He didn't even technically work there, but for the exchange of doing one show a night, he had acquaintances that would help him achieve the look he was looking for.

 

“Hey, Charlie,” Sam said to the drag king keeping a chart on who was next and what not. She was in a very nice Elvis suit, hair under a wig, but Sam still recognized her.

 

“Hey 'Doe', what's up?” Charlie asked and looked down at his suit case. “And more importantly, what have you got for me tonight?”

 

“Well...” Sam put his suit case on the nearby empty dressing station and pulled out a vintage 50's poster he'd printed out the day before, when he was planning it. Charlie raised a brow at the picture and took it to examine it further. The picture model had faux victory rolls and simple makeup. It was really something he'd been piecing together for a while. He liked the more refined things, but he wasn't exactly an expert at makeup or his own hair. He also didn't want to be too campy like several of the other costumes in the dressing room, nor was he going to play the catty drag queen behind stage either. He just, occasionally, wanted to dress up and feel beautiful for one evening. He didn't think it was a crime; just something rather deviant for a blooming lawyer.

 

“Mm, alright, suit up.” Charlie waved him off to get ready. “Let me see if we got any 50s songs around here. How do you feel about Marilyn Monroe?” Sam shrugged.

 

“'Diamond are a girl's best friend'?” Sam requested. Charlie gave him a thumbs up.

 

“Got it.” She made a note on her clip board and gestured for him to start getting ready. “I'll get a Ménage à Douze to help you with your hair and make up in a bit.” Sam nodded and opened his suitcase, getting ready to prepare for the show. 

 

 

* * *

 

Gabriel did not frequent the drag shows as much as he should, he decided as he entered the building. A grin pulled at his mouth as he watched someone go by in glitter and feathers. Man or woman, they looked so good doing it. Gabriel wasn't one to participate in the activity, but he could admire what a touch of makeup and the right clothes could do for a body. It was the illusion in itself that made it fun. How did one take an average male and make them look feminine? Somehow drag queens and female impersonators made it possible.

 

Most of the time, Gabriel found the costumes or makeup far too outlandish for even him to wrap his mind around, but what he didn't find sexy, he definitely found funny. Was he a bit of a pervert for checking out men in dresses? Probably, yes, but he didn't mind.

 

He found the bar and ordered a margarita. He put down money and looked around as he waited. A lovely Cher impersonator was singing on stage with extra colorful lashes. Gabriel saw others talking with customers, but one caught his eye as she -or he- slid up to the bar and asked the bartender for a drink. What caught his eye first was how absolutely tall  _ she _ was. She leaned down on the bar pretty far and she was only wearing 3 inch heels. Gabriel propped his head against his knuckles he slowly let his eyes slide up her body. The shoes, simple and black, contrasting with the white stockings. They were long, beautiful legs. The dress started a little above the knee, a vibrant red and black plaid that gave her hips a nice bell shape. Her waist was hugged by black fabric, giving it a nice defined look that Gabriel hoped beyond hope that it wasn't all padding. The bust and jacket matched the plaid skirt, but even the 50s shoulder pads wouldn't be an excuse for how much muscle she had in her torso; regardless of the fake breast bumps. Then there was the hair. Gabriel had no clue if it was a wig, but it was really gorgeous looking; the faux victory roll made from her bangs and the sides curled up to the back of her hair, allowing the rest of it to fall down her back, stopping at the shoulder blades. Her skin was powdered fair and her lips painted red. The eyes were embellished with a little pink eye shadow and very luxurious thick lashes. It was like she'd stepped out of an old pinup from the 50s.

 

Then the bar tender gently nudged him for his drink and he shook his head, coming out of his stupor. He took out another bill and told the bar tender he'd pay for the one in red plaid's drink as well. Moments later, she was handed her drink and Gabriel got pointed out. Gabriel gave her a charming smile and her eyes widened as she fixated on him. But after a stalled moment she gave a small, wave back, an awkward smile in place. It wasn't usually what he got in response, but he took it as an invitation anyway and moved to take a seat next to her.

 

"You look like you could be in the movies," Gabriel said with a smile. 

 

"Tha-" She cleared her throat, which gave away its depth before she spoke with a bit of a softer tone, "Thank you." She was definitely a he, but Gabriel wasn't going to get caught up with such a small detail like that. "For the drink, I mean."

 

"Couldn't help myself, really. Name's Gabriel," he said. 

 

"Doe Adeer," she returned.

 

"Doe a deer?" Gabriel's mind immediately flashed to one of his favorite songs to annoy his brothers with. She seemed to have heard it enough because she rolled her eyes and her lips pursed together.

 

"Yes, doe a dear, a female deer." She rolled her wrist in a way that made her seem much more flamboyant and so very evident that she did not want the line sung to her. "It was the first song I could sing here, so it sort of... stuck."

 

"Well you have very pretty eyes for a doe," he complimented and her eyes flickered down to her glass.

 

"You do realize I'm a man, don't you?" Doe asked and Gabriel gave her an easy going shrug.

 

"Yeah, kinda guessed it was a possibility since I'm in a drag bar. Pansexual, if you must know." Gabriel sipped his drink. "How about you, I'm not barking up a straight tree, am I? Cause that would be incredibly disappointing." She slowly seemed to relax and she took the seat next to him. He was not disappointed when she crossed her legs, very lady like.

 

"Bisexual," she said. Her voice was starting to relax from its soft state, becoming more masculine, but that certainly didn't affect the illusion before him. A wider smile spread on his lips.

 

"Lucky me." Gabriel had the itch to run a hand down the slightly extended leg.

 

"But that doesn't mean I'm looking for a pick up," Doe said firmly.

 

"Ah, break my heart why don't you." Gabriel pouted. A small smile creased her mouth and she sipped her drink through a straw so as to not smear her lipstick. "So then what are you here for, my deer?" Her eyes glanced around and she gave a small shrug.

 

"The party, I suppose," she said.

 

"Do you sing?"

 

"You missed it if you didn't see it already."

 

Gabriel snapped his fingers. "Damn. When do you go up again?"

 

"Not tonight, I'm relaxing the rest of the night."

 

"Would you mind some company?" Gabriel offered.

 

She was quiet a moment, but ultimately she nodded. "I guess some company would be nice."

 

 

* * *

 

They moved from the bar to one of the small tables when the bar became too crowded. Sam wasn't sure if he could keep up the charade in front of Gabriel. It was so nerve wracking. Every time Gabriel looked at him, he thought Gabriel was going to realized it was him and the whole thing would fall apart. Gabriel just smiled at him and Sam didn't know it was such an entrancing thing. It was obvious to everyone that he was a man in drag, but Gabriel was treating him better than a man in drag. He treated Sam like a woman and honestly if he thought on it too much, he would freeze up and his head would spin.

 

"Sweeping floors and fixing radiators doesn't sound very exciting," Sam said, his glass empty and he denied it being refilled earlier because it was very inconvenient to go to the bathroom in drag. Plus he didn't want to interrupt the conversation they had; full of witty comments and dancing around his real identity. 

 

Gabriel's smile was unwavering. "It's one of the best jobs I've ever had actually. I mean, no college loans to pay off. I got an apartment and a dog. And I get to tease the pretty lawyers in their own offices."

 

"Pretty lawyers?" Sam raised a finely manicured brow. He knew most of the other lawyers in the building were older men, but he couldn't be sure what Gabriel was into.

 

"Okay,  _ one _ pretty lawyer." Gabriel shrugged and his smile turned more sly. "Let's just say I know how to fix a radiator just enough so it will break every week or so." Sam blinked and it occurred to him that his radiator certainly did seem to break every week or so and he had to call Gabriel to fix it.

 

"That's um..." He wasn't sure whether to call it underhanded or blame Gabriel for not doing his job right, but he reminded himself he was Doe Adeer. Instead he found himself saying, "You must like him... or her."

 

"Him," Gabriel waved his hand idly. "Believe me, he's pretty, but he's also pretty convinced he's straight. I mean, he still has a picture of his ex-girlfriend on his desk." Sam internally winced when he thought of the picture of Jess he still hadn't moved. She hadn't taken well to his... hobby. She was embarrassed for him when he told her. She was then embarrassed  _ about _ him and couldn't understand why Sam couldn't just stop crossdressing. She had the assumption that he was mentally ill for wanting to put on nylon and heels. It wasn't exactly a good ending. "Does that make me sound too much like a pervert?" Sam realized he went quiet for a little too long.

 

"You're talking to a drag queen," Sam said, suddenly self conscious of his own desires. "Perversion is in the nature of what I do."

 

"Oh?" Gabriel cocked his head curiously. "Is this something you get off on?"

 

"Not physically." Sam folded his hands in his lap, trying not to pick at one of the red nails. A chip in the plastic was bothering him. "It's not really a stimulation. It's not a job. It's a recreation. I feel... relaxed." He pursed his lips briefly. "It's hard to explain, but I guess it doesn't matter. I'm still a man in a dress."

 

"If it's any consolation, you make a damn fine woman. Period." Gabriel some how sounded genuine and Sam felt weakened because of it. Perhaps the fleeting attraction towards the maintenance man from his law firm had grown within the past hour; much faster and deeper than in the months that he'd known Gabriel.

 

"Thank you," Sam said quietly, throat wet. He decided he needed a topic far away from a raw nerve like that. "So... you just work maintenance for the eye-candy. You don't have any future plans?" 

 

Gabriel shrugged, leaning back in his seat. "Nah, I haven't really wanted to move or anything. I mean, if I really wanted to do something else, I'd go back to Vegas."

 

Sam raised his brows curiously. "I suppose you like the flashing lights and dancing girls."

 

Gabriel laughed lightly. "Guilty. Also I do very well at the blackjack tables." 

 

Sam rolled his eyes. "Of course, a gambler. I knew you had a flaw somewhere."

 

A wide grin spread on Gabriel's face. "Are you insinuating I didn't have one before, my deer?"

 

Sam felt his face heat up and was so very happy for all the makeup he was wearing. "Of course not." He wished he could come up with some examples, but he couldn't. He didn't mind when Gabriel broke up his days of paperwork with a visit or bought his drink for him at the bar. He certainly didn't mind Gabriel liking him as a drag queen. Though the reason for him staying at the firm felt a little stalker-esk, and yes, a little perverted, it was a little comforting to know he wasn't the only one that did perverted things.

 

Gabriel continued on, "Well, even if gambling is a flaw, it's a rather profitable flaw. Especially when you count cards."

 

"Ah, so you're a felon. That explains a lot," Sam said mildly, keeping the mood light.

 

"It's not illegal. It's just _very_ frowned upon." Gabriel didn't seem offended.

 

"Of course." Sam nodded.

 

"So Doe, what do you do outside of drag?" Gabriel finally asked. Sam was stuck for a moment, because he really truly did not think he could tell anyone in his work life about what he did every month or so.

 

"Well... normal... non-drag things of course," Sam said. It would be easier to keep stories straight if he just didn't tell Gabriel about himself.

 

Gabriel pouted. "Aw, come on, I've told you everything about me. Even showed you pictures of my dog."

 

Sam had to admit Max was a cute dog, but it was far from the first time he'd seen the pictures. The new ones were good though; even Gabriel's dog was a ham. Sam had always wanted a dog, but with the long hours at the office, he didn't think it would be fair to the pooch he picked. "I'm flattered, really." Sam's heart beat faster and his hands squeezed tighter together. "I just..." He wasn't sure how to say it nicely. "You are nice company, but I'm not required to tell you anything about me."

 

"Touche'," Gabriel breathed out and propped his chin on his fingers, looking Sam over slowly. It was another one of those moments where Sam felt Gabriel's golden brown eyes were seeing right through his costume. Recognizing him. "Let me guess, I'm not your type?"

 

Sam quickly shook his head. "No, no, it's not like that. I..." What made it so hard was that Gabriel was beginning to be his type, but he couldn't tell Gabriel it was him. He couldn't let him know he was cross dressing. "I like to keep this," he rested his fingers on the table, indicating the bar, the lip syncing, the dress up, the mask itself, "separate from anything else."

 

Gabriel sat quietly for a moment, seeming to mull over his words. "Are you married then?" 

 

Sam laughed, more nervously than anything. "No, I'm not married."

 

"Then you were hurt," Gabriel guessed. Sam went quiet, remembering Jess and how he felt so bad about his hobby after he told her. He didn't feel he could be in another relationship and tell them about what he did. He realized he couldn't have both and he didn't want to have to make that choice again when he loved someone. "Sorry. Bad subject?"

 

"It's..." Sam blinked his eyes, he didn't need mascara running; he didn't want to look pathetic over something so long ago. Six months still felt like yesterday. "Raw still." 

 

Gabriel nodded slowly, thankfully not prying any further. "So, how often do you do this?"

 

"Um, every month or so." Sam pursed his lips. "You're not going to try to stalk me here, are you?"

 

"Well, if I can't know who you are out of drag, I'd still like to visit and keep you company." Gabriel gave him a warm smile and Sam really hated his stomach for doing that fluttery thing when Gabriel said things like that.

 

"I would like that," he found himself admitting.

 

 

* * *

 

Gabriel felt like bragging the Monday after. He didn't get laid, but he definitely felt like he had hit the jackpot with the drag show last night. Doe was a beautiful woman, drag queen or not. A sophisticated lady, and sassy at the right moments. Even though Doe had raw nerves over revealing who she/he was, Gabriel wanted to show her that he was not going to have a problem with her in women's clothes, but he also wanted to make it clear he was not in it for friendship. He wanted to take her somewhere nice. Maybe on a date. Woo her. Offer to help her undress in the sexiest way possible.

 

He told himself to keep a moderate pace. She was a deer; timid about letting people in. Gabriel wasn't afraid of a little challenge though.

 

Gabriel dressed for work and peeked in on Sam when the the place was quiet. He knocked on the open door as Sam was fiddling with paperwork. Sam glanced up and smiled a little when he did.

 

"Nothing's broken today, Gabriel," Sam told him, per usual as a greeting.

 

"Better not be or I'll accuse you of tampering with the heater to get me to come down here." Gabriel walked in and he felt something was missing from Sam's desk almost immediately. Sam rarely decorated his desk. It had been the same for the past year or so. "Hey, where's your picture?" The silver plated frame of Jess was gone from it's half hidden point behind the pencils. Sam fiddled with his pen between his fingers and he sighed, rubbing his palm over his jaw.

 

"Yeah I.... I mean, we haven't been together for a long time. She's not coming back. Time for me to get rid of her picture, right?" He looked up with the slightly watery doe eyes, as though unsure if that was the right answer.

 

"Yup." Gabriel nodded and leaned his hand on the desk, giving him a smile. "Why Sam, that's down right healthy." He laughed a little because it had been a little sad with Sam still holding onto a little 5 by 7 picture of Jess' smiling face. "Finally ready to move on?"

 

"I guess." Sam put his fiddled pen down and folded his hands together

 

"You should let me take you to a drag show," Gabriel teased. "Tons of lovely women there." Sam shook his head, ears and cheeks gaining a lovely shade of red.

 

"No thanks," he said quickly.

 

"Shame,” Gabriel said and Sam looked up at him, leaning back in his chair.

 

"You look, um... happy today," Sam guessed quietly. A grin spread across Gabriel's face.

 

"I met the most beautiful woman in the world last night while you were reading your book," Gabriel said whimsically.

 

"Woman?" Sam raised a brow.

 

"Yes, Sam, a woman. You do remember what a woman is, right?" Gabriel asked as he leaned his hip heavily against Sam's desk. Sam's brows stayed raised, as though he could sense Gabriel was leaving details out. "Well, okay, she's a drag queen, but that hardly matters."

 

"A drag queen?" Sam asked.

 

"Hey, not just ones in sparkles and feathers but well..." Gabriel waved his hand because there was so much more to Doe than a silly makeup mask and a dress. She had style and beauty. "Trust me, there are drag queens, and there are ladies, and when lines start blurring... well, let lines blur, I say. It's not just a man in a dress you know, it's the illusion." Sam's face fell a bit.

 

"An illusion. A mask right?" Sam's hands squeezed together. "It's not... real."

 

Gabriel thought about it. "Well, you  _ could _ say that," he frowned, "but you know, illusions are part of someone too. Sometimes the mask someone put on shows more about what's inside than the day to day one does." Sam didn't respond, he just stared at Gabriel like he didn't really know him. "What you staring at Sam?"

 

"I um..." Sam broke eye contact. "You really should do something else besides being a maintenance man." 

 

Gabriel chuckled. "Then who would fix your radiator?"

 

Sam frowned. "You could do so much more."

 

"I don't want to do more," Gabriel said simply. "I like it here. I got a nice place. I got a nice tree to bark at for the moment." He smiled, thinking of Doe and her pretty eyes. "I have a beautiful woman to visit in a couple weeks." Sam gave him a sympathetic look, as though Gabriel was acting pathetic. "What? I can't help it if I'm in love." All humor fell from Sam's face. He actually started to look pale after a moment.

 

"Love?" Sam asked dryly. "Didn't you just meet him last night?"

 

"Hm, yeah, so?" Gabriel smiled. "Come on, you know the butterflies and the shallow breathing thing. Fine, maybe it's just a crush, or what ever you want to call it. But all I know is I fell head over heels for a gorgeous brunette with long ass legs and eyes that could melt your soul." Maybe it came out more pathetic or poetic than he intended, but he didn't care, he was still swimming in the moment of meeting a woman out of his dreams. "Sue me for feeling gooey emotions." Sam had an underlying distress about him, arms folding across his chest.

 

"It's fine, I suppose." Sam pursed his lips, looking nervous. "But it's really a man under all the makeup and stuff. You know that, right?"

 

"... So?" Gabriel frowned. "It doesn't matter to me. I'm a pansexual. But she's portraying a woman, so she's a woman unless she shows me otherwise."

 

"Do you even know..." Sam sighed, unable to finish his question.

 

Gabriel quirked a brow at him. "Look, if it makes you uncomfortable, I won't talk about it."

 

Sam blinked, confused. "What?"

 

"If two guys hooking up makes you uncomfortable just say it and I'll stop talking about it," Gabriel said plainly. He liked Sam; really sexy eye-candy and he liked talking to him, but he didn't need to be continually reminded that Doe was really a man. He knew it, he didn't really care. Sam had never shown squeamishness to the subject before, but then again he hadn't talked deeply about perhaps-maybe being in love with one in front of him before.

 

"Oh, no, it's not that," Sam said quickly. "It's  _ not _ ," he reaffirmed when Gabriel gave him a raised brow of disbelief. "I just think... when the mask comes off, the illusion won't be there anymore. It sounds like you're really happy that he's a woman, but you know... won't you be disappointed when he's not?" Gabriel blinked.

 

"No," he said simply. Sam gave a frustrated sigh. "You do know what being pansexual means, don't you?"

 

"You're attracted to both sexes," Sam said with a frown. "Isn't it just a broader term than bisexual?"

 

Gabriel made the sound of a game show buzzer when the answer is wrong, startling Sam a little. "No. It means I'm attracted to people regardless of their sex or gender identity. You went to big fancy lawyer school, you took a course or three in psychology, didn't you?"

 

"Criminal psychology," Sam muttered. 

 

"Sex psychology is way more fun, take a course or two why don't you?" Gabriel said. "Look, there's sex and gender. Sex is the outside bits that people worry about when they're making babies. Gender is whether they feel more feminine or masculine or neither. There is a neither." Sam sat back and listened, looking curious. "Admittedly, I'm more attracted to the female gender, the more lovely but fiery personality. But it doesn't matter what sex that certain person is. I suppose, it's like, I have a type, but it's not an easy one to see." Sam nodded slowly.

 

"Oh," was all he said, but it seemed to get through to Sam. He looked at least a little more enlightened but then he grew nervous again. "But, you know, what if the person is masculine too?" Gabriel shrugged.

 

"As long as the person isn't a raging asshole, they'll probably still be sexy to me," Gabriel said. After a moment he snapped his fingers as he remembered an example. "I met your obnoxious brother once, he was a bit of a turn off." Sam smiled and chuckled softly.

 

"Yeah, well..." Sam looked from his hands back to Gabriel. "I just don't want you to get hurt if they turn out not to be what you expected." Gabriel smiled.

 

"Aw, you're sweet, all protective of me." Gabriel leaned forward and pinched Sam's cheek. 

 

Sam swatted his hand away. "Stop it, I hate when you do that." Sam rubbed his cheek giving him a glower. Gabriel gave him a smile.

 

"You know, you're pretty cute too, Sam," Gabriel told him and Sam went quiet. Gabriel rolled his eyes. "Yes, fine, don't hit on the straight guy. Sorry for making you uncomfortable or any sexual harassment or..."

 

"I'm bi," Sam said flatly. Gabriel paused, waiting for Sam to follow macho protocol and follow up with a joke but he didn't. He looked at Gabriel, calm but still nervous.

 

Gabriel folded his hands together and pleaded, "Please tell me I'm your type." 

 

Sam rolled his eyes, but there was a lovely blush on his face. "What about your drag queen that you're in love with?"

 

Gabriel smiled sheepishly. "Can I help it if you're both my type? I mean, I don't even know who she really is." He laughed to himself. "You're not a drag queen in disguise, are you, Sam?" Sam looked suddenly more uncomfortable but Gabriel waved it off. "Nah, you're not the type to go around in a dress, are you. Big macho lawyer and all." Sam sighed, looking tired of the conversation or perhaps disappointed. Gabriel slid off of Sam's desk. "Well, guess I should do my rounds."

 

"Yeah..." Sam tapped his fingers on the desk. "Gabriel?"

 

"Hm, what is it kiddo?" Gabriel stopped in the office door. 

 

"Um... good luck," Sam told him. Gabriel gave him a smile.

 

"Thanks, though I won't need it." He gave Sam a wink. "I have all this glorious skill to unleash." He gave a final  wave, Sam giving him an amused smile.

 

 

* * *

 

As the weeks passed, Gabriel's thoughts were still turned to Doe Adeer. Though they were also mixed with the joke he'd made about Sam being a drag queen in disguise. He didn't try to think about it, it just popped up often enough to get his attention. Sam and Doe were tall and both very beautiful. But they were very different. Sam was a quiet man who kept to himself. He was very professional and tight lipped. Honestly, Gabriel thought he could use a lesson in fun. Sam never talked about himself; sure Gabriel knew about Jess because of the neon sign that was the picture on Sam's desk; the only homey touch to Sam's otherwise clean-cut way of keeping his area neat. Sam had tried putting his brother's picture on the desk, but one client had commented about Sam's 'partner' and the picture quickly went back into storage. It was sort of hilarious when Gabriel heard about it.

 

Sam tried to keep up masculine appearances, and he did well at it too. Crisp suit and calculated mannerisms. Sure his hair was long, but it only just barely brushed his shoulders and it was brushed back to be neat and he certainly didn't get complaints from his clients about it.

 

But Doe was a lady. A classy woman with sway in her walk and a relaxed tone about her when they were talking. Not only was she beautiful but intelligent and sassy. She talked with Gabriel on more of a friendly level than Sam ever did. But she also didn't reveal anything about her home life or family. Even his dog pictures didn't pry anything but a friendly smile from her; and Max was usually his trump card.

 

Coincidently, Sam and Doe were both bisexual. If Gabriel thought had about it enough, he thought he saw some hand gestures that could have been the same, but he wasn't so sure now because he'd only spent a few fleeting hours with Doe. He hoped that Doe would be there on the same night she said she would be. There weren't as many tall people as her or Sam. What were the chances of two people being THAT gigantic, having some of the same facial structures, and both being his type?

 

Gabriel entered the bar and it only took him seconds to find Doe. She was tall and impossible to miss while talking to another, more flashy drag queen in white feathers. Doe was breath taking in dark green, styled like an ancient Greek dress. The fabric draped down in lovely folds and a gold belt pulled it in at the waist to give her more feminine definition. The neck dipped down to her breast line, enough to see her strong collar bone. At her shoulders were a couple broaches that appeared to be small golden deer. The shoulder fabric also covered her upper arms but then she wore long white gloves to her elbows, giving them a slimmer look. The heeled sandals she wore sometimes peeked out from the folds of fabric, but not often. Her hair was weaved in waterfall braids that extended from one temple down the other side of her neck, but didn't hinder the soft waves that rested against her shoulder blades. 

 

“Excuse me ladies,” Gabriel said with charming flare. “Hope I'm not interrupting anything.” Doe gave him a shy smile but the one decked out in glitter an feathers gave Doe a pat on the arm.

 

“Oh, not interrupting a thing. Doe here was just chatting about you,” Miss Feathers said in a mild British accent and drifted back into the crowd before she should see the deadly look Doe thew at her. Gabriel grinned.

 

“Oh, talking about me?” Gabriel asked, because that gave him some very hopeful prospects.

 

“They...” Doe sighed. “Saw us talking and assumed it was a date or something.”

 

“Well, it was sort of date-esk, wasn't it?” Gabriel slid his hands into his pockets. “We were sitting at the window, sort of talking for hours.” Doe nodded, her gloved hands clasping in front of her. That night she had a soft pink lipstick, but her eyeshadow was green, only accentuating the color in her eyes. He remembered then, didn't Sam have green or brown eyes? “So, do you want to get out of here and actually go on a date?”

 

Doe blinked those big eyes at him, looking very much caught in the headlights. “You're joking.”

 

“I'm offended that you would tease about such a thing,” Gabriel said lightly. “I know a diner that makes the best pancakes at midnight.” Doe pursed her lips, brow crinkling and Gabriel wondered if it really was Sam, how he got such perfect brows as a lady.

 

“I can't,” Doe said. “And I certainly don't think I'd pass on the street.”

 

“I think you would.” Gabriel encouraged. “Though I suppose that dress is far too fancy for a diner. But I think the kinds of restaurants that would do you justice is the kind that takes reservations.”

 

“Gabriel, I can't go out on a date with you,” Doe said more firmly, but looked regrettable at the same time. 

 

Gabriel frowned, confused. “Why not?”

 

She look a deep breath. “Look, I know you probably have some romantic notions towards me but I'm not...” She gestured to herself. “This isn't really me. I'm not a woman. This is an illusion; a mask.” Gabriel held his breath because Sam had said the same thing weeks before.

 

“So... what if it is?” Gabriel asked. “I don't think it's as big of a mask as you say it is. I think it's part of who you are. I mean, what if you're also a hot lawyer, who likes dogs, but doesn't think his hours will allow for one?” Doe's breath hitched and if anything she looked ready to bolt. Gabriel took her clasped hands gently, trying not to drive her away. “And what if, you know, you just tossed out that picture of your ex the other week and now your desk is really boring because the picture of your brother just brought up a lot of awkward questions from your clients?” Doe's eyes were on the floor, not denying the accusation. She probably had a clue that he guessed right. “Sam.” Her eyes flickered back up to his and he gave her a smile. “It's okay.”

 

“It's not okay,” Doe murmured.

 

“Yeah it is.” Gabriel nodded to one of the tables. “Come on, lets have this chat while we're comfortable.” Doe stood stalk still for a moment, but with a light pull she followed him to the table that they'd sat at weeks ago, her shoulders tense.

 

“How... long did you know?” Doe asked when she was seated.

 

“Well, I was thinking about it for a couple weeks, but I couldn't be sure until I met up with you again.” Gabriel smiled, his hand still on one of hers on the table. “You clean up good, Sam.”

 

“Please don't call me that here,” Doe said stiffly.

 

“Sorry,” Gabriel said. She relaxed a little as silence fell. She took her hand back, but seemed less likely to bolt as she composed herself. “You okay?”

 

“... yes and no,” Doe admitted quietly. “I didn't want anyone to know.”

 

"Well it is one fine skeleton you keep in the closet," Gabriel joked lightly. Doe didn't smile. She just looked at her connected hands quietly for several minutes. "Talk to me, Doe. Why are you so scared of me liking you?" Her eyes lifted to his under long lashes.

 

"The last person that I told about this was Jess," she said quiet enough that the bustling people nearly drowned her out. "She tried to be okay with it for a while, but then she told me to stop, and it was either her or the drag. And um," the tips of her gloved fingers touched, "I picked dresses and makeup over her."

 

"Well, I like you in and out of drag," Gabriel reminded her. "That's got to count for something."

 

"It does. Thank you," Doe said shyly, eyes focusing on her fingers. Gabriel weaved her fingers with his, the silk sliding nicely between his digits. "I..." Her eyes darted up again and she took in a breath. "Did you mean it when you said you loved me?" Gabriel blinked, having completely forgotten he'd said that during his and Sam's conversation. He could see where it may have come off a bit fast.

 

Gabriel squeezed her hand. "I'd like to, but I think I got to get your ass on a date first." She smiled, just for a moment. A jazzy tune started up and Gabriel nodded to the stage. "But hey, right now, you're a sexy lady, I'm a gentleman, and I want to dance with you." Doe blinked, confused as Gabriel stood. "Don't worry about it. Let's just have some fun." He extended a hand and she took it, standing up. 

 

“I think we're avoiding the conversation,” Doe said.

 

“I think it's an unfair conversation because I told you that when I didn't know it was you.” Gabriel pointed out and Doe looked guilty for it. Gabriel held her hand and lifted it up, kissing the back of the glove. “Make it up to me by dancing with me.”

 

“Is it really necessary?” Doe asked, allowing Gabriel to pull her to her feet.

 

“ _Absolutely,_ ” Gabriel said, slowly guiding her to a clearer area away from the chairs and bar. “Consider this the first date, in fact.” A slow smile spread on Doe's painted pink lips and Gabriel pulled her close, wrapping an arm around her waist. Her fingers re-weaved with Gabriel's and let him lead the dance.

 

“One dance,” Doe agreed to, but Gabriel was sure he could wiggle out a couple more before the night was through. 

 

 

* * *

 

Sam emerged from the back stage door into the alley-way. His suitcase was packed back up for the night and he returned to his normal male attire. The makeup was wiped away and he was so relieved to be back in sneakers again. He passed Mr. Golem and said good night to him, before he then looked to Gabriel, who had been standing with Mr. Golem since Gabriel was not allowed back stage. Gabriel lit up when he saw Sam, hands in his pockets.

 

“I'll have you know, dancing in heels is harder than it looks.” Sam told him as Gabriel followed him towards the parking lot.

 

“And I'll have you know you look damn fine doing it,” Gabriel returned. Sam was tired, but at the same time, relaxed. He didn't think he'd be okay after Gabriel found out, but felt good. It was all the more better that Gabriel hadn't freaked out like Jess had. “So,” Gabriel said once they got to Sam's car and Gabriel found a place to lean his hip into the side of the trunk. Sam popped open the trunk to put his suit case away. “Do I get to come too, or should I just eagerly await you Monday in your office?” Sam thought about it, closing his trunk.

 

“Well... I suppose it's early.” Sam folded his arms and then he felt how hungry he was. “We could get something to eat.”

 

Gabriel snapped his fingers and pointed at Sam. “I like the way you think.” He walked around the car to the passenger side of the car, inviting himself along for the ride. Sam smiled and clicked the button on his keys to unlock it. “I don't suppose I'll get to see you in one of those fine gowns outside of the drag show?” Sam thought about it a moment and then smiled as he got into the car.

 

“Maybe if you play your cards right, I'll put on my little black dress,” he said slowly. He was still trying out the words in public, but the more he thought about it, the more he liked the idea of it. Gabriel opened the passenger door and stared at Sam with wide eyes.

 

" _ You _ have a little black dress, my deer?" Gabriel hopped into the car, shutting the door after him.

 

Sam smiled, settled in his seat and started the car. He used his softer Doe voice, " _ Sweety _ , every lady has a little black dress." A slow and wide grin spread out on Gabriel's face as he made himself at home in the passenger seat.

 

“Oh please, do go on,” Gabriel said and Sam found himself smiling as he drove out of the parking lot; the neon sign of “ Hoo-Doo Yoo-Doo” glowing in the rear window.

 

* * *

 

 

[Colouragainstthewall's "Sam's little black dress"](http://coloursagainstthewall.tumblr.com/search/Sam+Winchester/page/2)


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